The 2020-21 season marked Garland's second in the NBA and second with the Cavaliers. He set career highs essentially across the board. In 33.1 minutes per game, the point guard averaged 17.4 points, 6.1 assists, 2.4 rebounds and 1.2 steals. He shot 45.1 percent from the field, 39.5 percent from three and 84.8 percent from the free-throw line. His 6.1 dimes per game ranked 18th in the NBA, and his 30.9 assist percentage ranked 19th in the league. Garland had six double-doubles. His best performance of the season came April 5 in a win over the Spurs. Garland scored a career-high 37 points (14-22 FG, 5-10 3Pt, 4-4 FT), seven assists, two steals and one block in 30 minutes. He handed out a career-high 12 assists in a win over the Pistons on Dec. 26. Garland swiped a career-high four steals April 28 against the Magic. He grabbed a career-high six rebounds Dec. 23 against the Hornets.

Garland was selected with the fifth overall pick in the 2019 NBA Draft by the Cavaliers. The Vanderbilt product made his NBA debut during the first game of the season, Oct. 23 against the Magic. Garland started, played 32 minutes and recorded eight points (3-9 FG, 2-4 3Pt), five assists, two rebounds and one steal. In his 59 appearances, the rookie averaged 12.3 points, 3.9 assists and 1.9 rebounds in 30.9 minutes per game. He shot 40.1 percent from the field, hit 1.8 threes per contest while shooting 35.5 percent from behind the arc, and shot an impressive 87.5 percent from the free-throw line. On Nov. 22, the young guard scored a career-high 23 points, plus added four dimes, during a loss at Dallas. His longest streak of double-digit scoring was 15 games from Dec. 28 through Jan. 25. Across that stretch, Garland averaged 14.9 points on 13.7 shots, 4.9 assists, 1.7 rebounds and 1.0 steals in 34.4 minutes. On Jan. 14, Garland double-doubled in a road game versus the Clippers. In that game, he posted 14 points, a career-high 10 assists and one steal. During the pandemic-shortened season, Garland had 14 games win which he hit three or more three-pointers. Twice Garland hit five three pointers in a game.